
Kid-friendly holiday rentals in Monterey
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Top-rated family-friendly rentals in Monterey
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Popular amenities for Monterey family-friendly rentals
Kid-friendly house rentals

Beautiful, quiet and cozy home in Becket!
My wife and I stayed here 2 night with our dog and had a great time. The cabin was super cozy and had everything we needed during our stay. Special shoutout to the couch, which was extremely comfortable for late night movie watching! If you are looking for a quiet weekend away to do some hiking, I would certainly recommend staying here. The town of Becket is very rural and food options can be somewhat limited but the house has a full kitchen and grill to use if that's more your style. Overall 5 stars would stay here again.

Berkshires Retreat | Fenced Yard + Near Tanglewood
Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.

- Lake Front 4 Bdr w/ Fast Internet! -
My family and I loved our stay. Jaryn was a wonderful host and the views from the house were incredible.

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

New Shaw Pond Skytop Retreat in the Berkshires
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

Berkshire Ski House on Lake Garfield W/HT By GB
This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.

A sunny, quiet chalet beautifully decorated.
Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.

Prime location for the best of the Berkshires
Marty’s cabin is perfect for a Great Barrington getaway. We stayed in the cabin for a ski weekend, and it simply met all our expectations and then some. The cabin was kept extremely clean and had a ton of extras (board games, coffee, filtered water, etc.) that added a great touch. Location was perfect for a day at butternut mountain. Highly recommend, and will definitely go back next year. Thank you!
Family-friendly apartment rentals

West Main
We stayed here on a weekend trip to Lime Rock and it was a great location! Close to the racetrack and also near the town center, as well as a relatively short drive to Great Barrington. The house was exactly as described and very clean, I would recommend it!

Amenia Main St Cozy Studio
Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.

Serene Suite by Gt. Barrington, Hudson, Tanglewood
We booked last minute to stay for a night to attend an event nearby. While our stay was brief, it was super clean, comfortable, and just what we needed. Everything smelled fresh, and Kelly’s recommendations were helpful too.

Quiet getaway in the Berkshires
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

Private Berkshire Barn Apartment
Just perfect: cozy, inviting, private. Everything you need, with lots of personal touches. We had a wonderful time!

The Beer Diviner Brewery Apartment
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

Modern Copake Falls Getaway - 8 Mins to Catamount
My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

Stunning studio in the heart of Troy: Raven's Den
Perfect night for a nearby getaway while things done at my apartment. Lot of charm and everything you could need is in this den. Pictures did it justice. I’ll stay again just for the fun of it next time. Igor was easy to communicate with and he was spot on with everything he has posted on the listing. This place is a gem!
Family-friendly apartment rentals

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Posh Pad in The Business District
We loved our stay at Obi’s apartment in Hartford. It was spacious and comfortable for our family of 4. Street parking was easy. Obi is a great host! We’d love to stay here again the next time we’re in the area.

Spacious 3 bedroom apt in Lenox historic downtown
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

New Britain "Joy of Small Space" Condo
Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!

Elegant, spacious studio apt in historic mansion
Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

Cozy & walking distance to cafés *spring avails*
Cozy apartment, walking distance from the water front. Had a great weekend getaway.

Downtown Condo - walk to MoCA
My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

Jiminy Peak Country Inn - ski in/out condo MT view
Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.
Quick stats about holiday rentals that are kid-friendly in Monterey
Total rentals
20 properties
Nightly prices starting at
₹7,707 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Six Flags New England
- TPC River Highlands
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- Kent Falls State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Norman Rockwell Museum
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag
- Mount Southington Ski Area